I actually wrote my MA thesis on the philosophy of fun but I've had a few new thoughts since I graduated. In short, 'fun' as a distinct concept is undertheorised in philosophy, instead thinkers tend to talk about 'play', 'leisure', 'games', 'pleasure' and so on.

What makes something fun though? Why is playing a game considered fun, while eating a nice meal, on the other hand although pleasurable, is rarely considered fun?

I think I have an idea. It first relies on making a distinction between 'generals' and 'specifics'. I think 'essential' and 'accidental' properties gets at a similar idea, as does 'universals' and 'particulars', but I'll show you where my mind is at when I use my terminology seeing as universal/particular and accidental/essential already come with a lot of baggage:

I think ‘folk’ use actually tracks my general/specific meanings pretty well but perhaps we can be clearer. In philosophy we sometimes speak of the difference between de re and de dicto. If I were to say ‘I’m going to marry the tallest man in New Zealand’, then this could be read one of two ways. A de re reading of ‘I’m going to marry the tallest man in New Zealand’ is that there is a specific man that I’m going to marry, say Jim, and ‘the tallest man in New Zealand’ picks him, and only him, out. Alternatively we can have a de dicto reading of the sentence where you are taken to mean that you do not have anyone specific in mind to marry when you say ‘I’m going to marry the tallest man in New Zealand’ but just have a taste for tall men with Kiwi accents so you aim to marry whoever fits the description at this time. In this case ‘the tallest man in New Zealand’ doesn’t represent a specific man but what I call a ‘general’: best seen as an non-specific idea of the tallest man.

I suggest this type of ‘specific’ and ‘general’ occurs quite widely in the use of English and not just in these ambiguous cases. One clue is that ‘generals’ can exist in a potential way, such as the idea that there is more than one person who could be the tallest man in New Zealand’: say Jim, and also Jack who - when Jim moves to Melbourne - is the new tallest man in New Zealand. Thus we see if the term is ‘specific’ there is only one tallest man that is picked out, but if it is ‘general’ sense there are multiple potential people that are the tallest man.

Another way of looking at ‘specific’ and ‘general’ is through the lens of change. I would say ‘the ball’ is specific in ‘the ball is red’ because we're talking about a specific ball while ‘red’ is ‘general’ seeing as other things could be red beside the ball. This also seems to fall along change/unchanging lines too. I could say ‘the ball’ is unchanging in what it refers to, while ‘red’ can change what it refers to, perhaps paint or pencils or trucks at a another time (having the potentiality of a ‘general’). Similarly, we can see how ‘the tallest man in New Zealand’ in the de dicto sense can change from Jim to Jack, but in the de re sense latches on to a specific person in an unchanging way.

OK, so here's the meat of my claim:

Fun is a semantic distinction rather than a terrestrial one. Sentences with 'specific' verbs can be ‘a pleasure’, sentences with 'specific' verbs and 'specific' objects can be ‘pleasurable’ while 'general' (either verbs or objects) can be ‘fun’.

Lets look at the following. The first thing to note is that when a verb is specific and thus 'unchanging' it doesn't mean that it is somehow static. It just means that it is a specific instance of that action, rather than in general.

(Eating with you) is a pleasure (specific verb no object)
(Talking to you) is a pleasure (specific verb no object)
(Eating chocolate) is pleasurable (specific verb with specific object)
(Drinking wine) is pleasurable (specific verb with specific object)
(Drinking Champagne) is fun (specific verb with general object)
(Thinking about my wedding) is fun (specific verb with general object)
(Watching football) was fun (specific verb with general object)
(Playing video games) is fun (specific verb with general object)
(Jogging) is fun (general verb)

So the difference is that video games, football, Champagne and thoughts about my wedding necessarily change from moment to moment (and are therefore objects that are 'general' as I define it) so can be fun. Wine and chocolate do not necessarily change from moment to moment, so are 'specific' and thus can be pleasurable. Jogging, too, as an activity, changes from instant to instant and is 'general', and can be fun, HOWEVER an instance of jogging, almost by definition, does not change from instant to instant so is 'specific' and not fun. I suspect this is why one would say ‘jogging IS fun’ in the general case yet it more unusual to say ‘I HAD fun’ about a specific instance of jogging (‘having fun’ it seems to me to do with a 'specific' instance of fun rather than 'general' cases).

What do you think of the theory? Does it track the fun/pleasurable distinction as you see it?